Look out for concealed functional group relationships
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص714-715
2025-07-12
549
Look out for concealed functional group relationships
The analgesic doxpicomine is a more difficult problem than those you have seen so far. At first sight it has no useful disconnections, especially as there are no carbonyl groups. However, removal of the acetal reveals a 1,3-diol that could be formed by reduction of a much more promising diester.
The diester has a 1,3-diCO relationship and could be disconnected but we have in mind using malonate so we would rather disconnect the alternative 3-amino carbonyl compound (the Me2N group has a 1,3-relationship with both ester groups) by a 1,3-diX disconnection giving an unsaturated ester. This α,β-unsaturated ester disconnects nicely to a heterocyclic aldehyde and diethyl malonate.
The synthesis is shorter than the retrosynthetic analysis and involves only four steps. Good retrosynthetic analysis, using two-group disconnections, should lead to short syntheses.
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